2-Phenylglutaric anhydride → 4-{3-[2-(2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)ethyl]-1,2,4-oxadiazol-5-yl}-2-phenylbutanoic Acid

HRID 585547Notes

Reaction equation

HRID 585547 reaction equation
[CH3:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]2[N:18]=[C:17]([CH2:19][C:20]3([CH2:25][C:26]([OH:28])=[O:27])CCCC3)[O:16][N:15]=2)=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[N:3]=1.[C:29]1(C2CCC(=O)OC2=O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH3:1][C:2]1[C:11]([CH2:12][CH2:13][C:14]2[N:18]=[C:17]([CH2:19][CH2:20][CH:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:26]([OH:28])=[O:27])[O:16][N:15]=2)=[CH:10][C:9]2[CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 962932-Phenylglutaric anhydrideHCID 10207073HCID 10207073, compound

Product 1

HCID 102796284-{3-[2-(2-methyl-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)ethyl]-1,2,4-oxadiazol-5-yl}-2-phenylbutanoic Acid

Procedure

The procedure for the preparation of the product of EXAMPLE 8 was repeated using 2-phenylglutaric anhydride (Aldrich) in the place of 3,3-tetramethyleneglutaric anhydride to provide a 55:45 mixture of the title products as a gum. 1H (CD3OD) δ 1.90 (2H, m); 2.15-2.35 (2H, comp. band); 2.32/2.40 (3H, s); 2.42-2.53 (1H, comp. band); 2.69/2.76 (2H, t); 2.85 (1H, m); 2.92-3.04 (4H, comp. band); 3.45 (2H, t); 3.66/4.39, (1H, t); 7.23-7.40 (5H, comp. band), 7.44/7.52 (1H, s).

Workup

  1. customto provide

Sources & evidence

ORD record
ord-d8fb91d63cba46e0b0ade07e61c68928
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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